Tetrahydrofuran → HCID 86676709, compound

Participants

Reaction Steps

To a solution of the product from Example 1C (865 mg, 3.19 mmol) in anhydrous tetrahydrofuran (30 mL) was slowly added a tetrahydrofuran (10 mL) solution of (2-carboxyethyl)triphenylphosphonium tribromide (1.85 g, 3.19 mmol) at 0° C. The mixture was then stirred at ambient temperature for 2 hours. The mixture was partitioned between ethyl acetate and water. The layers were separated, and the aqueous layer was washed with additional ethyl acetate. The organic fractions were combined, washed with brine, dried (MgSO4), filtered, and concentrated. The residue was chromatographed on silica gel eluting with 10% ethyl acetate/hexanes to provide the title compound: 1H NMR (300 MHz, CDCl3) δ ppm 2.31 (s, 3H), 2.37-2.27 (m, 2H), 3.60 (t, J=6.4 Hz, 2H), 4.11 (t, J=5.8 Hz, 2H), 5.42 (s, 1H), 6.90 (d, J=8.8 Hz, 2H), 7.36 (d, J=8.8 Hz, 2H); MS (DCI/NH3) m/z 366 (M+NH4)+.

Provenance & Evidence